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Volume 2003
Issue 4
10.3390/M344
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Short Note

1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone

by
Aryan Younessi
1,* and
Gennady D. Krapivin
2
1
Research Laboratory of Furan Chemistry, Kuban State University of Technology, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
2
Department of Organic Chemistry, Kuban State University of Technology, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(4), M344; https://doi.org/10.3390/M344
Submission received: 31 March 2003 / Accepted: 18 June 2003 / Published: 22 June 2003
Versions Notes
1,4-Dihydropyridines are of interest because some of them exhibit various kinds of pharmaceutical activity [1,2,3]. So in the course of our study we have synthesized novel derivatives of 1,4-dihydropyridine based on the reactions of furaldehydes with acetylacetone.
Molbank 2003 m344 i001
A mixture of acetylacetone (5.0 g, 30 mmol), furfural (2.4 g, 25 mmol) and CH3COONH4 (1.25 g, 16 mmol) in 20 mL of ethanol was refluxed for 5 h (the reaction duration was monitored with TLC) and left overnight at room temperature. Then solvent was evaporated, residue was washed with water, dried and recrystallized from ethyl acetate - hexane mixture to yield 3.19 g, 77 % of titled compound as pale yellow crystals.
Mp: 159-160 °C.
IR (KBr): 3300, 3230, 1675, 1665 cm-1.
1H NMR (acetone-d6, 60 MHz, ppm): 2.23 (s, 12H, 4 CH3), 5.15 (s, 1H, HA), 5.85 (d, J3,4 = 3.2, 3-HFur), 6.13 (d, J4,5 = 1.8, 4-HFur), 7.20 (d, J3,5 = 0.9, 5-HFur), 7.97 (s, 1H, NH).
Anal. calc. for C15H17NO3: C 69.48, H 6.61, N 5.40; Found: C 69.79, H 6.44, N 5.57.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

  1. Schleifer, K-J. J. Med. Chem. 1999, 42, 2204.
  2. Visentin, S.; Amiel, P.; Frittero, R.; et al. J. Med. Chem. 1999, 42, 1422. [PubMed]
  3. Jiang, J-L.; Li, A-H.; Jang, S-Y.; et al. J. Med. Chem. 1999, 42, 3055. [PubMed]
  • Sample availability: available from the authors.

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MDPI and ACS Style

Younessi, A.; Krapivin, G.D. 1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone. Molbank 2003, 2003, M344. https://doi.org/10.3390/M344

AMA Style

Younessi A, Krapivin GD. 1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone. Molbank. 2003; 2003(4):M344. https://doi.org/10.3390/M344

Chicago/Turabian Style

Younessi, Aryan, and Gennady D. Krapivin. 2003. "1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone" Molbank 2003, no. 4: M344. https://doi.org/10.3390/M344

APA Style

Younessi, A., & Krapivin, G. D. (2003). 1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone. Molbank, 2003(4), M344. https://doi.org/10.3390/M344

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